—
The gem in the collar was a yellow that came close to brown, not quite matching the honey colour of Simon’s hair but complimenting it nicely, especially with the gold in the chain itself.
It looked just right on Simon, Theodore thought as he clipped it on the boy in front of the mirror. It was too bad Simon wouldn’t stop marring his pretty face with tears. “Aren’t you going to at least open your eyes and take a look?”
Simon shook his head, whimpering.
Theodore sighed, hands running down Simon’s bare chest, watching their reflections in the mirror. His skin was so soft, so soft. “This is unlike you, Simon. You’re so brave normally.”
It was working, Daniel’s suggestion. But not tonight. Nothing could make poor Simon stop crying tonight. And Theodore wanted to respect that, give him more time. He wanted Simon to feel comfortable with him, like the other boys did. But he couldn’t wait any longer. He needed Simon in his bed tonight.
Theodore’s need pressed into Simon’s back as he held the boy tighter, caressing his soft skin. “That’s okay,” Theodore told him in a sigh. “I’ll show you it’s nothing to be afraid of. I won’t hurt you. You’ll even enjoy it.”
Simon just shook his head again, but this was something about which Theodore happened to be an expert. So he took Simon’s soft penis in one hand and started to stroke it gently, gently kissing the sides of his neck as he did. He played with Simon’s nipple as well, which got a gasp out of Simon.
Theodore noted that. He liked to know where his boys were sensitive.
Though he may not have wanted it, Simon was hard after a minute or so, and Theodore fixed his grip, and started masturbating the boy properly. “See?” he whispered, just loud enough to be heard over Simon’s crying. “It’s not so bad. You’re enjoying this more than you think you are.”
“No,” Simon sobbed, shaking his head again. “No. I don’t like it…”
“I think you do,” Theodore said, rubbing himself against Simon’s backside.
Simon was young and healthy and it only took him five more minutes to prove that he was enjoying it, body tensing as he came, semen splattering the mirror in front of him. Theodore watched his reflection as he orgasmed, his sadness wiped away by ecstasy for just a moment, one, precious moment.
Then Simon started crying even harder, and Theodore sighed. “Come,” he said, pulling away form Simon. He’d have happily rubbed himself against the boy until he came as well, but Theodore was a long way from that yet—the tears were making it harder—and he was impatient. “Surely it wasn’t that bad?”
But Simon, it seemed, had nothing to say, just standing there crying. It was…frustrating.
So, with a sigh, Theodore led him to the bed, lay him there. Simon complied, never resisting or fighting. He did everything Theodore bade him—except for stop crying.
Theodore spread Simon’s legs and poured oil on both his own hand and Simon’s member, still hard but softening. He took hold of that and got it to full strength again quickly, stoking Simon again as he inserted his fingers one at a time for stretching. He was patient and deliberate but not too slow. “See?” he asked, as he started sliding his fingers in and out. “It doesn’t hurt, does it?”
Simon didn’t respond except with a sniff, his eyes still shut. He was clenched so tightly around Theodore’s fingers. “You must relax,” Theodore cautioned. “Or else it will be very difficult.”
“I don’t care,” Simon whispered. “I don’t care. I don’t want…ah…”
Theodore shook his head, pressing against Simon’s prostate. Eventually, if it felt good enough for the boy, he’d calm down and realize it wasn’t as bad as he’d made it out to be in his imagination. Doubtless the other boys had filled his head with horror stories about what Theodore was like. He ought not to have let Simon spend time with them—especially with Daniel.
But there was nothing to be done about it now. Theodore would show Simon that he wasn’t to be feared. He kept stretching the boy, until finally he got used to it, his breathing evening out a little. Tears still ran down his face, but Simon had stopped resisting quite so much, and relaxed. Theodore was able to widen him properly, still masturbating Simon as he did.
When he’d deemed it was enough, Theodore withdrew his fingers, smiling down at Simon. “Now,” he said. “Don’t be afraid.”
He moved between Simon’s legs, taking his own member in hand and making sure it was covered in enough oil to make entry easy. Then he started to push inside. Simon let out a loud whinge of discomfort, trying to tighten around Theodore again, but Theodore kept going, too lost in the tightness inside Simon to pull away now.
Simon cried out louder when Theodore was most of the way in, another orgasm making its way through him thanks to Theodore’s hand. Theodore smiled, leaning down to kiss Simon. “Not so bad,” he said.
With no energy to do much but lay there, Simon just shook his head, eyes still shut. Theodore gave a push, entering the rest of the way into Simon with a gasp. Stroking Simon’s hair out of his eyes, Theodore began moving.
He slid in and out of Simon, losing himself in the pleasure of it, the boy writhing under him, oversensitive, perhaps. Theodore did his best to ignore Simon’s crying, focusing instead on pleasuring both of them—not only himself, but showing Simon that he could enjoy this part too. The boys all learned this eventually, once they stopped being afraid.
How long Theodore was inside of Simon he didn’t know. Simon’s crying was more of a distraction than he’d expected, which had the consequence of making Theodore last longer than he often did during this part. By the end of it he was covered in a sheen of sweat and tired with it, but he felt himself building to his orgasm and went slightly harder. “Not long now, Simon…”
Simon surprised Theodore then—he cried out something wordless, with the shape of a name, and he came again, finally opening his swimming eyes as if in shock. That alone was enough to drive Theodore over the edge, and he grunted as he finally hit his orgasm inside Simon.
When he was done, Theodore pulled out of Simon, stroking his hair, his face. “There, now. Seems you enjoyed that in the end, didn’t you?”
Simon shook his head, crying again. “No.”
“Very well,” Theodore said, sighing. He’d understand sooner or later. “Lying to yourself hurts only you, Simon. Let’s go have a bath.”
Simon wouldn’t move, so Theodore had to carry him. He was tired but satisfied. He felt like, despite the tears, he had made progress with Simon.
Simon would learn eventually. They all did.
—
How Best to Use a Sword 